Hydrogen Bromide → alpha-Hydroxyalprazolam

HRID 2296065Notes

Reaction equation

HRID 2296065 reaction equation
COC1C=CC(C[O:8][CH2:9][C:10]2[N:14]3[C:15]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:16]=4[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:18][CH2:19][C:13]3=[N:12][N:11]=2)=CC=1.Br.[OH-].[Na+]>C(O)(=O)C>[C:20]1([C:17]2[C:16]3[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:15]=3[N:14]3[C:10]([CH2:9][OH:8])=[N:11][N:12]=[C:13]3[CH2:19][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 204730871-[(p-methoxybenzyloxy)-methyl]-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 162244alpha-Hydroxyalprazolam

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3,0 g 1-[(p-methoxybenzyloxy)-methyl]-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine in 30 ml of glacial acetic acid is added at 25° 24 ml 48% aqueous hydrobromic acid. The reaction mixture is stirred for 20 minutes, neutralised with 30% sodium hydroxide solution and extracted with methylenechloride. The organic phase is separated, washed with water, dried over sodium sulphate and evaporated to dryness. The crystallisation of the residue from acetate-ether-petrol ether yields 6-phenyl-8-chloro-4-H-s-triazolo[4,3-a][1,4]benzodiazepine-1-methanol, M.P. 209°-211°.

Workup

  1. extractionextracted with methylenechloride
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe crystallisation of the residue from acetate-ether-petrol ether

Sources & evidence

ORD record
ord-934559f1cee24f87a3e64acc7d5fa532
Source dataset
uspto-grants-1984_01
Patent number
US04427590

Reaction notes

Loading…